Abstract
A synthesis is reported for N1-mono- and N1,N3-disubstituted uracil derivatives containing a terminal carbon-carbon double bond in the side-chain. Alkylation of vinyl 2-chloroethyl ether by uracil potassium salts leads to a mixture of 1-[2-(vinyloxy)ethyl] and 1,3-di[2-(vinyloxy)ethyl] derivatives while treatment of 2,4-bis(trimethylsilyloxy)pyrimidines by vinyl 2-chloroethyl ether leads exclusively to N1-monosubstituted products. Alkylation of cytosine by this chloroether gave 1-[2-(vinyloxy)ethyl]cytosine. The synthesis of 1-[2-(allyloxy)ethyl]uracil derivatives was carried out by treatment of uracil potassium salts by 1-(allyloxy)-2-(p-toluenesulfonyloxy)ethane.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 393–397, March, 1993.
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Novikov, M.M., Brel', A.K. & Ozerov, A.A. Synthesis of [2-(vinyloxy)ethyl]uracil and [2-(allyloxy)ethyl]uracil. Chem Heterocycl Compd 29, 330–334 (1993). https://doi.org/10.1007/BF00531511
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DOI: https://doi.org/10.1007/BF00531511